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View 6 Deer Island Homes for Sale

Below you can view all the homes for sale in the Deer Island subdivision located in Winter Garden Florida. Listings in Deer Island are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Deer Island, give us a call at (407) 444-0331.

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Viewing Homes 1 to 6 of 6

Deer Island | House For Sale $1,229,000

17569 Deer Isle Cir, Winter Garden, Florida 34787

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17569 Deer Isle Cir. Listed | 49 Days Ago
  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    6477

  • Year Built

    1991

  • $/SqFt

    $189

This grandiose, custom, lake-front English Tudor estate redefines what a dream home is. Nestled in the exclusive Deer Island gated community, highly esteemed for its privacy and comfort, with several pleasant walking paths, exclusive tennis courts, and gorgeous sights of John's Lake. As you're pulling in the long circular driveway, you are welcomed by beautiful mature oak trees and a stunning garden courtyard. The home has over 6,477 sq ft, with 6 bedrooms and 5/2 bathrooms, with immaculate high-end finishes throughout the house, including natural stone, brick, stained glass, and iron-accentuated solid wood doors. The master bedroom offers an oversized walk in closet, and a spa tub overlooking the lake. The kitchen features built in cabinetry and granite countertops that makes it all come together. The remainder of the bedrooms are upstairs, perfect for the family, with a loft area and game room, and views of the lake as well. As you step outside into the large lanai area, you will notice an outdoor summer kitchen and lounge, next to an amazing pool, perfect for entertaining. Spacious backyard with own private dock and oak trees to provide shade during hot summer days and the upmost privacy. Enjoy a hot cup of coffee in the morning as the sun rises on the eastern side. If you're looking for a private lake front home only a few minutes away from downtown, OIA, and the attractions, but yet tucked away for tranquility and peacefulness, look no further. Roof will be replaced; new roof is valued at $50,000. 5373427

Regal R.E. Professionals Llc

Deer Island | House For Sale $2,690,000

17683 Deer Isle Cir, Winter Garden, Florida 34787

Reduced By $510,000

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17683 Deer Isle Cir. Listed | 706 Days Ago
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    7429

  • Year Built

    2008

  • $/SqFt

    $362

You Waited -now Is The Time! Big Price Reduction From Motivated Seller! Gorgeous Furnished Lakefront Estate-custom Builder's Personal Home On Johns Lake (2500 Acre Lake!!) With Boat House, Lift For Boat & 2 Jet Skis! Large Lakefront, Heated Pool! Fabulous Lakefront Balconies & Sprawling Waterfront Terraces With Beautiful Statuary. Grand Covered Outdoor Living Area Boasts A Spacious, Covered Living "room" With Fireplace And Dining Area Which Seamlessly Opens From The Family Room. Deer Island Is An Intimate Gated Enclave Located In Winter Garden With Its Charming Tree-lined Downtown, Shoppes And The Charming Plant-street Market - The "new Windermere! Professionally Designed Interior With Fine Furniture Boasts Towering Ceilings And Waterfront Windows, Theater, Office, Lakefront Billiard Room! Outstanding Kitchen With 21' Granite Serving Bar Opening To Family Room With Entertainment Center & Large Screen T.V! 1st Floor Master Suite! Dramatic 2-story Staircase Leads To Secondary Bedrooms, Balcony And Lounge And More!!!!! Sound System! Wood And Stone Flooring Throughout! ! 4-car Garage! Owner's Second Home - Seldom Used- Looks New! Move In-start Living! You Must See This Before You Buy A Lakefront Home! Too Beautiful To Be Missed! Opportunity Awaits You In This Beautiful Setting! 5179765

* Potential Great Value

Oxford Realty, Inc.

Deer Island | House For Sale $1,110,000

17814 Westbay Ct, Winter Garden, Florida 34787

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17814 Westbay Ct. Listed | July 15, 2015
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2780

  • Year Built

    1999

  • $/SqFt

    $399

Lakefront living at its Finest. This lakefront home is located in the gated community of Deer Island on Johns Lake. The home is perfect for entertaining or for quiet relaxation in your own private screened room on Johns Lake. The home has video monitoring system, a new roof, extensive exterior and interior accent lighting and a volleyball court. The boat house has two lifts, one for a boat and the other for 2 jets skis. 5379919

Coggan Realty Llc

Deer Island | House For Sale $810,000

17802 Westbay Ct, Winter Garden, Florida 34787

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17802 Westbay Ct. Listed | July 27, 2015
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2752

  • Year Built

    1989

  • $/SqFt

    $294

Absolutely stunning lakefront home in Deer Island, a gated community of custom homes on John's Lake. 3/3 with a den/office that could be converted to 4th bedroom. This home has been completely remodeled inside and out. A full renovation was done in 2012. Upgrades include but are not limited to: Opening the floorplan up to a gorgeous open concept with a large yet homey feel, upgraded tile everywhere except the bedrooms which have carpet, stunning chef's kitchen, vaulted ceilings, crown molding in every room, enlarged master suite with a HUGE walk-in closet, all bathrooms remodeled with granite and custom tile, new plumbing, electrical, and AC ducting. Exterior features include brick paver driveway, new roof (2012), unbelievable covered and screened in patio with resurfaced pool and outdoor kitchen. The lot is over an acre and the spacious back yard features a covered boat dock with two jet ski lifts and a boat lift. All this less than 20 minutes from Downtown Orlando! This house is truly one of a kind. Too many upgrades to list. Full renovation details are available; inquire with listing agent. Schedule an appointment today! This lakefront dream home will not last long. 5382367

Re/Max Prime Properties

Deer Island | House For Sale $4,759,000

17819 Westbay Ct, Winter Garden, Florida 34787

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17819 Westbay Ct. Listed | 122 Days Ago
  • Bedrooms

    7

  • Full Bath(s)

    7

  • Sq. Ft.

    11650

  • Year Built

    2010

  • $/SqFt

    $408

Casa De Leon is the epitome of luxury Florida living. This custom built masterpiece is a must see for that buyer who’s looking for a one of a kind property. Privately situated on a 1.75 acre peninsula with panoramic water views from every room and over 700’ feet of lake frontage this home would be almost impossible to duplicate. This exquisite estate boasts 7 bedrooms (including 2 master suites), 7 baths, 2 half baths, a 5 car garage, and a 1,500 sq. ft. guest suite. The kitchen in this home was designed by a chef and features a massive center island, top of the line appliances, beautiful custom cabinetry, a hidden pantry, and sumptuous granite countertops. Absolutely no expense was spared in the construction of this home, from the energy saving features hidden behind the walls to the exceptional finishes found throughout every inch of this striking residence. As you step through the front door your breath will be taken away by the soaring ceilings, custom wrought iron railings, and floor to ceiling windows that frame the stunning lake views. Additional features include a library with rich wood details, a home theater, wine cellar, elevator, game room, exercise room, 8 person sauna, and a steam shower. Exterior amenities include a 70’ long infinity edge pool with Intellitoutch remote to control the spa and gas fire bowls, a boat house with jet-ski and boat lifts, and loads of patio space for entertaining. Rich with amenities and only 20 minutes from downtown no finer home is available for the price. 5357313

* Potential Great Value

Regal R.E. Professionals Llc

Deer Island | House For Sale $480,000

17508 Deer Isle Cir, Winter Garden, Florida 34787

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17508 Deer Isle Cir. Listed | 348 Days Ago
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4274

  • Year Built

    1996

  • $/SqFt

    $112

Short Sale. Bank approved price. Buyer is responsible for HOA and code enforcement payments of $6K total. 5314153

* Short Sale

Eureka Realty

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Viewing Homes 1 to 6 of 6